Trimethyl - hydroquinone condensa-



Patented Jan. 5, 1943 UNITED "STATES PATENT OFFICE John A. Aeschlimann, Riehen, nearBasel, Switzerland, assignor to I-loffmann-La Roche Inc., Nutley, N. J., a. corporation of New Jersey No Drawing. Application January 26, 1940, Seri al No. 315,854. In Switzerland February 16,

Claims. (Cl. 260-479) It is known that trimethyl-hydroquinone can of trimethyl-hydroquinone in 200 parts by Weight be condensed with phytol or with phytyl-halides of benzene and 40 parts by weight of anhydrous or phytadiene to dl-oc-COCOPhEIOl. zinc-chloride, dissolved in 450 parts by weight of It has now been found that a hitherto unknown dry ether, while stirring at 40 C. The product condensation product can be obtained if tri- 5 is gently heated under reflux for another 4 hours, methyl-hydroquinone is condensed with acetylthen treated with water, and the benzene-ether phytol. The resulting condensation product can layer successively Washed with water, dilute hybe transformed into a crystalline compound by drochloric acid, a dilute solution of caustic soda, acetylation. and several times with water. After drying with The intermediate condensation product is a sodium-sulphate, the solvents are distilled off. paste of the consistency of soft soap which is The residue consists of a soapy paste. The prodsoluble in petroleum-ether. It reduces potasnot is dissolved in warm petroleum-ether, wheresium-permanganate in the cold, and gold-chloby the condensation product precipitates as a ride in the heat. The acetyl derivative, obtained flocculent deposit on cooling. The solution is therefrom by treatment with acetic anhydride, 1;} centrifuged, the petroleum-ether decanted, and distils at 220 C. at a pressure of 0.08 mm.; after the residue dried in vacuo. 190 parts by weight recrystallisation from methyl-alcohol it shows a of a paste of the consistency of soft soap are melting point of 60 C. The iodine value is 48.9 obtained.

(calculated 49.4). It is not capable of reducing By acetylation with 1 parts by weight of permanganate or alcoholic silver-nitrate in the acetic anhydride at 140-160 C. an oil distilling cold. Its formula is: at 220 C./0.08 mm. is obtained which can'be CHa CH3 CH3 By hydrolysis with methyl alcoholic sulphuric 3U recrystallised from 3 parts by weight of methylacid an oil is obtained therefrom which reduces alcohol. White crystals of melting point 60 C.

gold-chloride, forms duro-hydroquinone by therare obtained. The substance has the empirical mal decomposition and is identical with dl-uformula: Cal-15404 of a diacetyl derivative of tocopherol. (HO)2Cs(CH3)3.C2oI-I39. C=76.8,H=l0.3. Iodine The condensation product is to be employed value=48.9. CH3CO=16.6%. Calculated: C= for the manufacture of medicinal preparations 77.0, H=l0.5. Iodine value=49.4. CH3CO= having the action of vitamin E, and as an inter- 16.7%. mediate in the preparation of further pharma- I claim: ceutically important compounds. 1. An acetylated trimethyl-phytyl-hydroquinone of the formula CH: CH: (iJHa x0 OHr-CH=J:-(omt-dH-(Crun-omomp-omcm Example wherein X is selected from the group consisting In the course of one hour, parts by weight of hydrogen and acetyl radicals. of acetyl-phytol in 200 parts by weight of ben- 2. An acetylated trimethyl-phytyl-hydroquizene are added to a mixture of 74 parts by weight none of the formula CH: 'Ha CH: omooo CHr-OElba-(CH2)PCH(OH2)s-( JH(CHa);0H(CHu) 3. An acety lated trimethy l-phytyi-hydroquiing the intermediate product with acetic anhynone of the formula dride.

CH3 I Process for the manufacture of a trimethyl- 5. 2,5,6-trimethyI-3-phyty1-benzohydroquinone hydroquinone condensation product, consisting of diacetate. reacting trimethyl-hydroquinone with acetyl- J OHN A. AESCHLIMANN.

phytol in presence of zinc chloride and acetylat- 

